We're well into the third season as the time of this writing, and many of the original cast are seniors getting ready to graduate. I imagine there will be some key episodes coming up, but I'm not known for my patience.
Key Episodes
The challenge in choosing Key Episodes for Glee is that each episode usually advances some kind of plotline, that important characters and plotlines rotate (the star of one episode will be standing in the background in the next), and that the characters' plotlines rarely interact much with each other. Except for the basic "we're preparing for a contest!" structure (and the contest episodes rarely advance other plotlines much), it's hard to identify one plotline as being more important than another.
Therefore, instead of choosing several key episodes for the story, I'm choosing one key episode for each character. (Episodes presented in chronological order and do not reflect the importance of the character; Rachel, for example, is probably the main character and appeared in a prominent role in many episodes before the one I chose for her.)
Will
1.1 "Pilot": Will takes over coaching the Glee Club; Rachel (Lea Michele) shows off as self-assured star; Finn (Cory Monteith), a shower-singing quarterback, resists joining the loser club. Notable music: The pilot is just packed with songs. Much of the cast sings audition songs that quickly sketch in their vocal talents and to some extent their personal arcs. Rachel belts "On My Own" from Les Miserables, Kurt also goes Broadway with "Mr. Cellophane" from Chicago, Mercedes sings "Respect" by Aretha Franklin, etc. The episode concludes with the iconic group performance of "Don't Stop Believin'" by Journey. I'm also a fan of rival club Vocal Adrenaline's ridiculous show-choired-up performance of "Rehab" by Amy Winehouse.
Quinn, Kurt
1.4 "Preggers": Head cheerleader and celibacy club president Quinn (Dianna Agron) discovers she's pregnant; Kurt (Chris Colfer) comes out to his father Burt (Mike O'Malley) and turns the football team into a bunch of fabulous dancers!! Music: Kurt teaches the football team to move to Beyonce's "Single Ladies (Put A Ring On It)."
Artie, Tina
1.9 "Wheels": Artie (Kevin McHale) is uncomfortable with the Glee Club's efforts to raise money for a wheelchair-accessible bus so that he can go with them to Sectionals; on a date with Artie, Tina (Jenna Ushkowitz) reveals a secret about her stutter; Will is suspicious of villainous cheerleading coach Sue Sylvester (Jane Lynch) when she invites Becky (Lauren Potter), a student with Down syndrome, to join the Cheerios; Kurt and Rachel compete for a solo. Music: Artie does a great poignant "Dancing With Myself" by Billy Idol, and Kurt and Rachel's cut-together one-on-one fight for "Defying Gravity" from Wicked is not to be missed.
Sue
1.15 "The Power of Madonna": One of several episodes with the "Sue's Diary" conceit, this one also ends with a rare musical performance from Jane Lynch: a shot-for-shot remake of Madonna's "Vogue" video. Music: All Madonna, all the time.
Rachel
1.18 "Laryngitis": Rachel freaks out when she gets laryngitis and can't sing. Finn introduces her to a permanently injured friend to give her perspective. For various contrived reasons, Kurt briefly dates Brittany and Puck briefly dates Mercedes. Music: Because Rachel is currently dating a guy called Jesse, Finn gets to sing Rick Springfield's "Jessie's Girl." I like Puck and Mercedes singing Frank Sinatra's "The Lady is a Tramp." Kurt does kind of a bad job at John Cougar Mellencamp's "Pink Houses" in an attempt to appear manly, and it's adorable.
Brittany
2.2 "Britney/Brittany": Delightful idiot cheerleader Brittany (Heather Morris) has Britney Spears-themed hallucinations while under dental anaesthetic. John Stamos guest stars as the dentist. Music: Mostly Britney Spears (including "Toxic" and "Slave 4 U").
Finn
2.3 "Grilled Cheesus": Finn questions his beliefs; Burt has a heart attack. Music: Finn's sensitive performance of "Losing My Religion" by R.E.M. is at the heart of this episode. Mercedes also gets to sing with a church choir, and Puck was born to sing Billy Joel.
Santana
2.15 "Sexy": Substitute health teacher Holly (Gwyneth Paltrow) encourages Santana (Naya Rivera) to express her love to Brittany, while the others learn important sex ed lessons. Music: Santana is visibly moved while singing "Landslide" by Dixie Chicks with Holly and Brittany.
Mercedes
2.17 "A Night of Neglect": Mercedes tries acting like a diva to gain respect from the Glee Club. Meanwhile, the Academic Decathlon team, which Brittany is somehow on, is raising money, and Will wants to perform songs by "neglected" artists.
Sam
2.19 "Rumours": Sam reveals that his family has been living out of a motel after their home was foreclosed on. Sue's new gossip rag spreads rumors about all the Glee Club members. Music: All of the music is from Fleetwood Mac's "Rumours" album, which actually works pretty well.
Mike, Emma
3.3 "Asian F": Mike's (Harry Shum, Jr.) father doesn't want him to dance; Emma's (Jayma Mays) parents, "ginger supremacists," visit, revealing the backstory behind her OCD; Mercedes feels unappreciated when she's asked to share her West Side Story role with Rachel. Music: Mike's dancing during "Cool" from West Side Story makes me want to stand up and cheer, while Will serenading Emma with "Fix You" by Coldplay makes me want to barf.
Puck
3.6 "Mash Off": Semi-reformed bully Puck (Mark Salling) falls in love with Shelby (Idina Menzel), the adoptive mother of his and Quinn's baby. Meanwhile, things heat up in the simultaneous and ridiculous student council president and state congressman race plots, and Santana is angry at Finn, who knows she's a lesbian. Music: Puck brings it as usual with Van Halen's "Hot for Teacher," and the two glee clubs battle with a bunch of mash-ups, notably "One Way Or Another"/"Hit Me With Your Best Shot."
Becky
3.10 "Yes/No": In the first and only episode with Becky voiceover--which switches from Lauren Potter's voice to Helen Mirren's--Becky has a crush on Artie and asks him out. Meanwhile, Finn finds out the truth about his father's death, and Will proposes to Emma. Music: Nothing very memorable, although I kind of like Sam and Mercedes singing "Summer Nights" from Grease.
Blaine
3.15 "Big Brother": Ex-private-school-boy and Kurt boyfriend Blaine (Darren Criss) is annoyed when his older brother Cooper (the ridiculously handsome Matt Bomer of White Collar) sweeps into town and charms everyone. A subplot has Quinn in a wheelchair or something, I don't know. Music: Blaine and Cooper have some good duets, particularly their Duran Duran mash-up of "Hungry Like the Wolf" and "Rio" (I love Rock Band), though I have to agree with A.V. Club's Todd VanDerWerff though, when he says, "Blaine has exactly one singing mode, and that’s needlessly confrontational, though smiling."
Bonus Episodes
1.5 "The Rhodes Not Taken": Entertaining guest spot by Kristen Chenoweth as a former glee club star whose life has only gone downhill. Music: Anything Kristen Chenoweth sings is great, but I'm especially fond of her Cabaret duet with Rachel.
1.6 "Vitamin D": The boys vs. the girls in "mash-ups." Will's insane/stupid wife at the time, Terri (Jessalyn Gilsig), gets the girls high on amphetamine pills and they deliver a delightfully manic performance. Music: Both mash-ups are good--the guys sing "It's My Life" by Bon Jovi mashed with "Confessions Part II" by Usher, and the girls sing "Halo" by Beyonce mixed with "Walking on Sunshine" by Katrina and the Waves.
1.11 "Hairography": The club tries to learn showy tricks to gain an edge over their Sectionals competition, and Quinn brings Puck on a baby-sitting job to test if he would be a good father. Music: Quinn sings the eerily appropriate "Papa Don't Preach." The club abandons "hairography" when they're reminded about heart by the School for the Deaf's moving sign language performance of "Imagine" by John Lennon.
1.13 "Sectionals": The club competes in their first event and has to create a whole new setlist at the last minute when the other teams steal their best songs, in one of the most exciting and solid episodes. Music: Rachel's (Lea Michele) almost-not-at-all-autotuned performance of "Don't Rain on My Parade" is particularly exhilarating.
1.20 "Theatricality": It's the girls vs. the guys as the club explores two artists who exemplify "theatricality," Lady Gaga and Kiss. (Kurt joins the girls' side.) Finn is mad at his mother for dating Kurt's father and takes it out on Kurt, leading one of the many Burt-emotionally-defends-Kurt moments. We learn the identity of Rachel's birth mother. Music: The guys sing some Kiss songs which I guess are fine. I don't really know Kiss. The girls-and-Kurt's "Bad Romance" is great, but Rachel and Shelby's "Poker Face" is just weird.
2.5 "The Rocky Horror Glee Show": It's a pretty bad episode, plot-wise, but all of the music is from Rocky Horror!!!1
2.8 "Furt": Finn's mother and Kurt's father get married; Sue marries herself; and Kurt leaves McKinley for the boys' prep school, Dalton Academy, because the school board refuses to discipline a boy for bullying him, and because Blaine is sooo cute. Music: This is not one of the episodes to watch for the music. There's a bunch of Bruno Mars.
2,14 "Blame it on the Alcohol": Blaine thinks he might be bisexual and kisses Rachel at a party. Kurt is upset. All the kids get to have fun playing drunk. Music: Various alcohol-themed songs, plus Rachel's stirring original composition, "My Headband."
2.20 "Prom Queen": Who doesn't love a prom episode? Music: Features a fairly decent all-guy rendition of "Friday" by Rebecca Black, and a sadly not-all-guy rendition of Abba's "Dancing Queen."
3.5 "The First Time": Rachel and Blaine star in the school's performance of West Side Story and Artie freaks out as director of the show; at a gay bar, former Dalton classmate and out-and-out villain Sebastian tries to win Blaine away from Kurt; Blaine and Kurt and Finn and Rachel consider having sex (I mean, not all together). Music: Mostly songs from West Side Story. Rachel and Blaine are both solid Broadway singers.
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